

The Pathless Path with Paul Millerd
Paul Millerd
The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.
Episodes
Mentioned books

Nov 10, 2021 • 1h 51min
Valuing Options & Possibilities On The Solo Creator Path with Kris Abdelmessih
Kris Abdelmessih has one of the most unique perspectives on life and works I've stumbled across in the past few years. He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models. I enjoy his perspective because unlike other financial types, he seems to have a proper appreciation of non-work / non-productive time.We explore his recent break from trading, his creative journey writing on the internet, and finding his people, and he challenges me to think differently about how I'm spending my time with my work.The conversation dramatically shifted how I'm thinking about the possibilities of my path. If you are on a self-employed path, this is a must-listen:For Kris' newsletter: Party at the Moontower - (moontowermeta.com)------------SUPPORT BOUNDLESSSubscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.If you'd like to support the podcast, consider using my affiliate linksPodia - 14-day free trialTeachable - 14-day free trialWealthfront - $5k managed for freeConvertKit - First 1k subscribers for freeCharles Schwaab No International ATM Fees
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Sep 27, 2021 • 1h 13min
The Formless Path - Money, Fatherhood & Creativity (Howard Gray)
Howard Gray is the founder of Wavetable, a studio that helps brands and companies come together to develop fan-based experiences to help teams teach and share ideas.
The two things that drive him are to "create space for people to do the work they want to do" and to help people "make sense of the world and overcome the tension of putting things out in the world"
We dive into his idea of the formless path, why the creator economy is in danger of being hijacked, how he sees himself as a guide rather than as a creator, and why fatherhood is helping him "sharpen" his focus.
Links Mentioned
Howard Homepage
Labels In, Labels Out
Jobs, Vocations, Careers
SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
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Wealthfront - $5k managed for free
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📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Sep 19, 2021 • 1h 4min
The Shadow Side of Solopreneurship - Darren Joe
“You can’t study or learn your way into a new identity” - I love this quote from Darren Joe. He’s been thinking about carving a different path from 2003 to 2004. He said that he was driven by a natural drive to be independent and do his own thing. I found this pretty impressive because in those years not many people were doing what he was doing.
He recently published a book titled The Fail-Safe Entrepreneur. In it he argues that almost all solopreneurs strive for three things: Freedom, Adventure, Meaning. I definitely agree. However, he says many fail to reach these aims because they ignore the shadow side of this path. He details four things - FAIL: Failure, anxiety, instability, loneliness.
We explore many things in this conversation including:
Grappling with the achiever identity
Longing for independence and freedom
Parental approval
Building Community
Experiments
Defining success
You can buy his book the Fail Safe Solopreneur on Amazon
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SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Aug 19, 2021 • 24min
Six Months In The Creator Economy - Michael Ashcroft (Part 3)
In parts 1 and 2, I interviewed Michael about his plan to quit his comfortable consulting job and start a new path creating and selling courses online.
Let's see how he reacts to his own quotes from a year earlier!
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📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Aug 4, 2021 • 58min
Accidental Freelancer To Brand Consultant, Founder & Freelance Coach (Austin Church)
Austin Church thought he was going to be a poet. When that didn't go as planned, he joined the business world. Six months later he was laid off in the 2008 recession. Luckily, his firm hired him back as a freelancer and that completely changed his perspective on work. Ever since he's been hacking a living, shifting roles as a freelancer, founder, entrepreneur, and coach. We chat about his journey and more.
Learn more about Austin and his great writing on freelancing here.
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SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Jul 22, 2021 • 59min
Burnout & "Living At Work" In 2020 - Natalie Rachel
Natalie Rachel went through her own experience with burnout before turning to help others. She found that "with burnout, rest doesn't touch it," you need a deeper strategy. We compare notes on our own journeys where we were surprised by burnout. We thought it was something that resulted from working long hours. Natalie says a better way to think about it is as "self-neglect of reflection."
Resources Mentioned:
Natalie On Twitter
Natalie on the James Altucher Show
Dr. Geri Puleo
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SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Jul 6, 2021 • 55min
Narratives, Work & What Matters - Ben Hunt
Ben Hunt is a father, husband, former academic, author turned blogger, former hedge fund analyst, investment advisor, and farmer.
And he’s also my podcast guest in this episode.
His writing has been an inspiration to me as I try to carve my own path after leaving what he calls “Team Elite.” His philosophy of make, protect, teach focuses on local and bottom-up change in the world. In addition, we also discuss:
How losing his father changed his relationship with time
Industrially necessary scripts and "the good egg"
Why writing about work elicits strange responses
How he thinks about narratives and politics related to work
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SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Jun 24, 2021 • 1h 4min
Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols
Jenni and Lisa Dazols read an essay six years ago which made them question their frantic & busy lifestyle. They could barely take care of their dog. They decided to take a break from a work. We dove into their story of deciding to move abroad, taking a sabbatical, having kids, moving to Taiwan, launching a passion project, coaching people on their money fears, and what they've learned along the way.
They run a business called Modern Family Finance and help people think about finances in a way that lets them live the life they want to live. They also run a charity bike ride in Taiwan supporting LGBTQ rights called Rainbow Ride.
Links:
Rushed and Tired (Portrait of a Modern Family)
Money Script Quiz
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Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
I'm launching a Freelance Consulting Skills Course that launches July 1. You can sign up here and get a $50 discount.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

13 snips
Jun 17, 2021 • 46min
A Sabbatical Every Seven Weeks - Sean McCabe
Sean McCabe runs seanwes and in 2014 he was working seven days per week. Yup, no breaks. He knew he needed to make a chance but the problem? All of his friends and even his wife worked at the company. He decided he would take every seven weeks off. He quickly realized it was a bit unfair to his team and extended it to everyone in the company. He's found that not only has his life gotten better but his business has continued to grow and they have figured out how to build mandatory (not like "unlimited vacation...) sabbaticals into the operating rhythm of the company. His mission is to help every company globally (yes, really) embrace this model by 2047. I'm on board.
Learn more about Sean
Sean's Sabbatical Blog
My Essay On Sabbaticals
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Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
I'm launching a Freelance Consulting Skills Course that launches July 1. You can sign up here.
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

29 snips
May 3, 2021 • 1h 2min
Ali Abdaal on Identity, Prestige, Creativity & Meaning and Deciding To Leave Medicine
I had a conversation with Ali Abdaal about his year away from medicine, how he grapples with his identity, the challenges of veering off the course of traditional metrics of success, enjoying the journey, and the challenges he faces.More from Ali here: https://aliabdaal.com/---------Subscribe to Paul's Weekly Newsletter: http://boundless.substack.com
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here